In 1985, he began his comedy career by following up on a suggestion by David Lawrence
(a disc jockey friend who had been paying Drew to write jokes for
David's radio show in Cleveland) to go to the library and borrow books
on how to write jokes.[5][6] The following year, after winning an open-mic contest, he became MC at the Cleveland Comedy Club.[2]
He performed at multiple comedy clubs over the next few years in both
Cleveland and Los Angeles. He was first brought to the national eye as a
comedian when he competed in the 1988 Star Search.[7] Carey was working as a stand-up comedian in 1991 when he appeared on The Tonight Show Starring Johnny Carson.[8]
His performance that night impressed Carson, who invited Carey to the
couch next to his desk; this was considered a rare honor for any
comedian.[5][9] In that same year, Carey joined the 14th Annual Young Comedians Special on HBO and made his first appearance on Late Night with David Letterman.[10] In 1994, Carey wrote his own stand-up comedy special which aired on Showtime, entitled Drew Carey: Human Cartoon, for which he won a CableACE Award for Best Writing.[11]

Following on the success of his early stand-up career, he
subsequently appeared in a number of supporting roles on television
shows, during which he developed the character of a hapless middle-class
bachelor. In 1993, Carey had a small role in the film Coneheads as a taxi passenger. Turning his attention to television, in 1994, Carey co-starred with John Caponera in The Good Life, a short-lived sitcom that aired on NBC.[12] After the show's cancellation, Carey joined up with writer Bruce Helford (who was also a writer for The Good Life), who gave Carey a job as a consultant for the television show Someone Like Me.[13]

After their stint on Someone Like Me, Carey and Helford developed and produced the storyline for The Drew Carey Show.
The sitcom revolved around a fictionalized version of Carey, as he took
on the stresses of life and work with his group of childhood friends.
The show premiered on September 13, 1995 on ABC. In his autobiography, Carey revealed his frustration with having to deal with censors and being unable to employ the off-color humor common in his stand-up routines.[4] Carey initially earned $60,000 per episode in the first seasons, then renegotiated for $300,000.[14] By the final season, he was earning $750,000 per episode.[15]
The show had high ratings for its first few seasons, but declining
ratings and increasing production costs (around $3 million per episode)
precipitated its cancellation.[15][16]
The program had a total of 233 episodes over its nine-year run and
Carey was one of four actors to appear in every episode. The show
starred (in order of episode appearances) Carey, Diedrich Bader, Kathy Kinney, Ryan Stiles (all in every episode); Craig Ferguson (starring role in seasons 2-8 and guest appearances in 9); Christa Miller (seasons 1-7); and Ian Gomez (semi-regular from seasons 1-9) and John Carroll Lynch (semi-regular from seasons 3/4-9).

While still starring in The Drew Carey Show, in 1998 Carey began hosting the American version of the improvisational comedy show Whose Line Is It Anyway?.
He would announce the improv guests, direct the games, and then would
usually involve himself in the final game of the episode. The show ran
for a total of 220 episodes until the show's cancellation in 2006. In
1998, the New York Friars' Club made Carey the newest inductee of the group's Comedy Central Roast. His friend Ryan Stiles (who costarred in The Drew Carey Show and Whose Line Is It Anyway?) served as the roastmaster.[17] Carey's income from Whose Line Is It Anyway? and The Drew Carey Show led to his inclusion on the Forbes list of highest-paid entertainers of 1998, at 24th with $45.5 million.[18]

On November 18, 2010, the Game Show Network announced that Drew Carey would host a new improv show in primetime, called Drew Carey's Improv-A-Ganza. The show is filmed at the MGM Grand in Las Vegas, Nevada and first aired on April 11, 2011.[21] The show takes on the premise of Whose Line? and Drew Carey's Green Screen Show in that it features many of the same performers from both shows and they do improv based on audience-provided suggestions.

Carey was one of the founders of the Improv All-Stars, a group of eleven actors who perform in unscripted skits.[22] The group joined Carey in all three of his improv shows, Whose Line Is It Anyway?, Drew Carey's Green Screen Show, and Drew Carey's Improv-a-ganza and some members had major roles or guest starred on The Drew Carey Show.[23] The Improv All-Stars travel on comedy tours, performing at comedy clubs throughout the United States.

Beginning in 2007, Carey began hosting game shows, beginning with his April selection as host of the CBS game show pilot Power of 10.
The show ran from August 7, 2007 to April 7, 2008 and aired twice
weekly during the late summer and early fall. Each game featured
contestants predicting how a cross-section of Americans responded to
questions covering a wide variety of topics in polls conducted by CBS.[24]

After taping the pilot episode for Power of 10, Carey was contacted by CBS about replacing the retiring Bob Barker at The Price Is Right. After initially turning down the offer, Carey announced on Late Show with David Letterman that he would succeed Barker as host of the program beginning in the fall of 2007.[25] His first episode of The Price Is Right
was taped on August 15, and his shows began airing on October 15. In
response to replacing Barker as host of the game show, Carey stated "You
can't replace Bob Barker. I don't compare myself to anybody... It's
only about what you're doing and supposed to do, and I feel like I'm
supposed to be doing this."[26] When Carey began hosting, the set, theme music, and show logo were updated. However, Carey kept the old closing line about spaying and neutering
that originated with Barker, although his version uses slightly
different wording. During Carey's second year as host, he began to write
some of the sketches used during the Showcase, which features guest appearances by stars of other CBS programs.

Carey began appearing in commercials for restaurants in the late 1990s in Canada with The Great Root Bear, but his two-year contract with A&W Food Services of Canada was cut short in November 1998 after an episode of The Drew Carey Show featured McDonald's. As a result of his dismissal, Carey sued A&W for compensation.[27]

Disney's Hollywood Studios (then "Disney-MGM Studios"), part of Walt Disney World Resort in Florida, debuted a 12-minute attraction in 1999 titled Sounds Dangerous!.[28]
In the show, a camera follows Carey through a day as an undercover
detective. When his video camera fails, the audience is left in complete
darkness wearing earphones, following his adventure through sound cues.
The attraction is presently running on a limited "seasonal" schedule.

In 2000, Carey was given a cameo appearance in the House Party expansion pack of the computer game The Sims.[29]
To make him appear, the characters in the game must throw a successful
party, which causes Carey to arrive in a limo and join the festivities.
Carey is a fan of The Sims series and during one April Fool's episode of The Drew Carey Show, a scene takes place completely within The Sims.[29][30] Carey made several other cameo appearances in music videos, including "Weird Al" Yankovic's "It's All About the Pentiums"[31] and Fountains of Wayne's 2004 video for "Mexican Wine", giving an introduction to the video as if it were on a stage.[32]

Although primarily known for his television work, Carey has done limited film work, with his first appearance in 1993's Coneheads. His next film was the 2000 television film, Geppetto that debuted on The Wonderful World of Disney. The film, an adaptation of Pinocchio, included actor Wayne Brady who had joined Carey on his improv shows.[33] Carey took singing lessons to prepare for the role.[3] In 2005, Carey appeared in three films: the animated film Robots, where he provided a voice-over for the character Crank; The Aristocrats where he retold a dirty joke along with other celebrities; and the documentary, Fuck, where he was interviewed.

Carey provided the entertainment for the 2002 Annual White House correspondents' dinner.[10] Once Carey completed his standup routine for the 1,800 guests, President George W. Bush, noting Carey's improv work, made a joke of his own: "Drew? Got any interest in the Middle East?"[34] In 2003, he joined Jamie Kennedy to host the WB's live special Play for a Billion.[35] In September 2003, Carey led a group of comedians, including Blake Clark and The Drew Carey Show's Kathy Kinney, on a comedy tour of Iraq.[36]